Montrose approached the 1974/75 season, the last of the two division Scottish League Championship, with some degree of confidence. Eighth place in Division Two in the previous campaign had seen manager Alec Stuart consolidate his side in the upper half of the 19 team league.

League reconstruction would see the top six in the division join up with the bottom eight in the old first division to form the new Division One. In anticipation of this and in order to achieve an even number of teams in the Scottish Leagues, Meadowbank Thistle were admitted to the league for the 1974/75 campaign.

Prior to the league season starting, there was League Cup business to attend to, played on a sectional basis, with other teams in the group to be played home and away. Montrose found themselves drawn against Kilmarnock (newly-promoted to Division One), Stranraer (who had finished a place behind the Gable Endies the previous season) and Queen's Park. The competition would also see an experimental modification of the offside rule, where players could only be penalised if within 18 yards of the goal-line.

However before the season kicked-off, headlines were made when striker Bobby Hutchinson was transferred to Dundee for a fee reported to be £20,000, thus exceeding the previous record fee received by the club (£19,000 from Notts Forest for Jim McIntosh in September 1970). Subsequent press reports put the figure even higher, at £22,000. Either way it wasn't a bad piece of business for the 21 year-old who had been signed two years earlier from Aberdeen Lads Club as a midfielder and had only been moved up front in the second-half of the previous season. Hutchinson went on to score on his debut against Celtic three days later in a Drybrough Cup tie and spent three years at Dens, before having another three years with Hibs.

Meanwhile, Montrose were about to set off on a Highland tour. Alec Stuart had a full squad available with the exception of defender Stewart Markland. The manager also called provisional signing Jim Guyan, an 18 year-old striker with Lewis United into the tour party as a replacement for Hutchinson. Travelling as a trialist was 23 year-old full-back Billy McManus who had just been released after six seasons with St Johnstone.

The tour opened with a 7-2 victory over Forres in which Harry Johnston starred, netting a hat-trick, whilst Guyan grabbed a brace. Kenny Cameron and Bobby Livingstone also got on the scoresheet. This was followed up with a 5-0 victory at Inverness Caley. Charlie Guthrie and the influential Cameron each bagged a double, whilst Les Barr rounded things off with a classic 20 yarder into the top corner.

In all, the club went through pre-season unbeaten (6 games) but manager Stuart had selection worries prior to the opening League Cup tie at Kilmarnock on Saturday August 10th. With Hutchison departed and Malcolm Lowe and Willie Lawson suspended, he only had 13 fit players to call upon and he indicated that he would be bringing yet another provisional signing from the Aberdeen juniors into his squad - 17 year-old Garry Craig from Banks O'Dee. It was also reported that Stuart had tried to buy back record scorer in a season Brian Third, who had been sold to St Mirren a year previously but who hadn't been enjoying the best of times there, as he was not being allowed to play in his favoured centre-forward berth. However the approach had been rejected and Stuart had to content himself with signing trialist McManus on a two month deal. He completed a 14 man pool that also contained two keepers in Dave Gorman and George Whisker.

Montrose lined-up: Gorman, Barr, McManus, Markland, D'Arcy, Watson, Guthrie, O'Donnell, Cameron, Livingstone and Johnston. However the vital ingredient missing from that selection was a natural finisher as the Gable Endies failed to take any of the many chances that came their way. In contrast, Killie were able to capitalise on their chances and ran out 2-0 winners courtesy of goals by Fleming and McCulloch. After the match, Alec Stuart hinted that he was still trying to bring back Third who hadn't been included in St Mirren's squad for their tie v Stirling Albion and that he would include youngster Craig for the home tie v Queen's Park on the Wednesday night.

Craig did indeed start against the Spiders replacing Markland, as Cameron dropped back into his preferred midfield role and John O'Donnell moved back to defence. Malcolm Lowe who had been the star of the Highland Tour also returned, replacing the unlucky McManus. A crowd of 850 had gathered in Links Park by kick-off but they had little to shout about on a damp night as Montrose's lack of fire power was again exposed, as Bobby Livingstone struggled to find his form. Both sides hit the woodwork early in the game - a Cameron header for Montrose - and though the homesters dominated for 90% of the game, their only other clear chance came late on when Barr who had pushed forward in place of Livingstone, cannoned a shot off the keeper's legs. It ended goalless, whilst Kilmarnock put themselves in a commanding position at the top of the group with a 5-0 win at Stranraer, a result that the Gable Endies would be delighted to emulate when they travelled there on the Saturday.

Without a goal between them in the competition so far, both Stranraer and Montrose were keen to make amends - and so they did! The visitors eventually ran out 4-2 winners. Though the only change for the Gable Endies was Markland for O'Donnell in defence, they were a transformed side, playing slick, flowing football against a stuffy home side. Gorman, Lowe and Johnston were outstanding, with the two Kennys - Watson and Cameron not far behind, whilst Livingstone was also back to form. Charlie Guthrie opened the scoring and grabbed another. Cameron also got in on the act and there was a first goal for Garry Craig, who was getting sharper with each game and looking like a decent replacement for Hutchinson.

Next up were Queen's Park at Hampden on Wednesday August 21st. Livingstone was a doubt with an ankle knock that had caused him to be subbed at Stranraer, but he was fit enough to take his place in an unchanged line-up. Montrose took a first minute lead through Craig who took advantage of defensive hesitation to knock home a Johnston cross. Johnston made it two just before the half-hour mark but the homesters contrived to make life difficult for themselves, when McGill crashed in Queen's first goal in four games in the 53rd minute. The response was instant however, as again Johnston set up Craig, who hammered home. That should have been it but there was an anxious last five minutes for the home fans when Thomson headed a second for the visitors. Montrose held on for the 3-2 victory which left them lying in second with five points from four games, three behind Kilmarnock who had a 100% record. With Killie's vastly superior goal difference, Montrose would have to beat Stranraer at home on the Saturday and hope that Queen's Park could pull off a shock win at Rugby Park, if the club were to make the knock-out stages.

Manager Stuart was looking to field an unchanged side against the Stair Parkers but he did have the bonus of Willie Lawson's four match ban being over. However, Kenny Watson failed a late fitness test and O'Donnell returned to midfield. Garry Craig opened the scoring - his fourth in three games - and his speed and ability to turn in tight spaces in the box, was drawing comparisons with Joe Harper. His goal settled Montrose who had been over-anxious up to that point and Harry Johnston - just back from Lords where he was playing cricket for Scotland v the MCC, scoring a commendable 45 in the second innings whilst batting at number 7 - who set up Craig, added a second to give Montrose a comfortable victory. However Killie's 6-0 win over Queen's Park meant that only pride would be at stake when the Ayrshire men visited Links Park four days later to round off the group stage.

Watson returned to an otherwise unchanged line-up on the Wednesday evening and played in Craig (yet again) for a 62nd minute equaliser to cancel out a 30th minute opener from Ian Fleming (the top scorer in Scotland at the point with 9 goals from 6 games, and later to become manager of Brechin City). Craig limped off shortly after, but the visitors were lucky to share the points as Livingstone, the ever-impressive Cameron and Guthrie all had chances to win it for Montrose. However had it not been for two excellent saves from Gorman early in the second-half, the game may have been beyond the Gable Endies reach before Craig's goal. As it was, they were left to rue their slow start to the competition and focus on their opening league fixture against East Stirling, three days later.